Cu-catalyzed endo-selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with ethenesulfonyl fluorides: Efficient access to chiral pyrrolidine-3-sulfonyl fluorides
Cu-catalyzed endo-selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with ethenesulfonyl fluorides: Efficient access to chiral pyrrolidine-3-sulfonyl fluorides
复制标题
铜催化的偶氮甲碱叶立德与乙烯磺酰氟的内选择性不对称1,3-偶极环加成：有效获得手性吡咯烷-3-磺酰氟
DOI：
10.1016/j.cclet.2021.05.063
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发表时间：
2021-12-01
影响因子：
9.1
通讯作者：
Wang, Chun-Jiang
中科院分区：
文献类型：
--
作者：
Li, Yi-Nan;Chang, Xin;Wang, Chun-Jiang
成功开发了铜催化的甲亚胺叶立德与乙烯磺酰氟 (ESF) 的内选择性不对称 1,3-偶极环加成反应，该方案为多种手性吡咯烷-3-磺酰氟提供了一种高效、简便的方法，并取得了良好至优异的结果（产率高达 87%，>20:1 dr，94% ee）。一些其他手性磺酰基衍生物，例如磺酰胺和磺酸盐，可以通过简单的转化轻松获得高产率，这表明环加成产物可以在硫（VI）氟化物交换（SuFEx）化学中合成有用。 (C) 2021 由Elsevier B.V.代表中国化学会和中国医学科学院药物研究所出版。
Cu-catalyzed endo-selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with ethenesulfonyl fluorides (ESFs) was successfully developed, this protocol provided an efficient and facile method to a wide range of chiral pyrrolidine-3-sulfonyl fluorides with good to excellent results (up to 87% yield, >20:1 dr, 94% ee). Some other chiral sulfonyl derivatives, such as sulfonamide and sulfonate, were easily accessible through simple transformations with high yields, which demonstrated that the cycloaddition products could be synthetically useful in the sulfur(VI) fluoride exchange (SuFEx) chemistry. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.